diff --git a/src/main/java/com/hubspot/jinjava/lib/exptest/ExpTestLibrary.java b/src/main/java/com/hubspot/jinjava/lib/exptest/ExpTestLibrary.java
index b14dc8451..087ef2ed5 100644
--- a/src/main/java/com/hubspot/jinjava/lib/exptest/ExpTestLibrary.java
+++ b/src/main/java/com/hubspot/jinjava/lib/exptest/ExpTestLibrary.java
@@ -43,6 +43,7 @@ protected void registerDefaults() {
       IsFloatExpTest.class,
       IsStringExpTest.class,
       IsStringContainingExpTest.class,
+      IsStringMatchingRegexExpTest.class,
       IsStringStartingWithExpTest.class,
       IsTrueExpTest.class,
       IsFalseExpTest.class,
diff --git a/src/main/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTest.java b/src/main/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTest.java
new file mode 100644
index 000000000..3a90be46d
--- /dev/null
+++ b/src/main/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTest.java
@@ -0,0 +1,79 @@
+package com.hubspot.jinjava.lib.exptest;
+
+import com.google.re2j.Matcher;
+import com.google.re2j.Pattern;
+import com.google.re2j.PatternSyntaxException;
+import com.hubspot.jinjava.doc.annotations.JinjavaDoc;
+import com.hubspot.jinjava.doc.annotations.JinjavaParam;
+import com.hubspot.jinjava.doc.annotations.JinjavaSnippet;
+import com.hubspot.jinjava.interpret.InvalidArgumentException;
+import com.hubspot.jinjava.interpret.InvalidReason;
+import com.hubspot.jinjava.interpret.JinjavaInterpreter;
+import com.hubspot.jinjava.interpret.TemplateSyntaxException;
+
+@JinjavaDoc(
+  value = "Return true if object is a string which matches a specified regular expression " +
+  "(Java RE2 syntax). Uses partial matching (the pattern can match anywhere in the string). " +
+  "Anchor with ^...$ for full-string matching.",
+  input = @JinjavaParam(value = "string", type = "string", required = true),
+  params = @JinjavaParam(
+    value = "regex",
+    type = "string",
+    desc = "The regular expression to match against the string",
+    required = true
+  ),
+  snippets = {
+    @JinjavaSnippet(
+      code = "{% if variable is string_matching_regex '[0-9]+' %}\n" +
+      "      <!--code to render if variable matches regex -->\n" +
+      "{% endif %}"
+    ),
+    @JinjavaSnippet(
+      desc = "Use with selectattr to filter a list by regex",
+      code = "{{ items|selectattr('name', 'string_matching_regex', '^foo') }}"
+    ),
+  }
+)
+public class IsStringMatchingRegexExpTest extends IsStringExpTest {
+
+  @Override
+  public String getName() {
+    return super.getName() + "_matching_regex";
+  }
+
+  @Override
+  public boolean evaluate(Object var, JinjavaInterpreter interpreter, Object... args) {
+    if (!super.evaluate(var, interpreter, args)) {
+      return false;
+    }
+
+    if (args.length == 0) {
+      throw new TemplateSyntaxException(
+        interpreter,
+        getName(),
+        "requires 1 argument (regex string)"
+      );
+    }
+
+    if (args[0] == null) {
+      return false;
+    }
+
+    String regex = args[0].toString();
+
+    try {
+      Pattern p = Pattern.compile(regex);
+      Matcher matcher = p.matcher((String) var);
+
+      return matcher.find();
+    } catch (PatternSyntaxException e) {
+      throw new InvalidArgumentException(
+        interpreter,
+        this,
+        InvalidReason.REGEX,
+        0,
+        regex
+      );
+    }
+  }
+}
diff --git a/src/main/java/com/hubspot/jinjava/lib/filter/FilterLibrary.java b/src/main/java/com/hubspot/jinjava/lib/filter/FilterLibrary.java
index f5dfc30e3..17cb46bd2 100644
--- a/src/main/java/com/hubspot/jinjava/lib/filter/FilterLibrary.java
+++ b/src/main/java/com/hubspot/jinjava/lib/filter/FilterLibrary.java
@@ -87,6 +87,7 @@ protected void registerDefaults() {
       PlusTimeFilter.class,
       PrettyPrintFilter.class,
       RandomFilter.class,
+      MatchesRegexFilter.class,
       RegexReplaceFilter.class,
       RejectFilter.class,
       RejectAttrFilter.class,
diff --git a/src/main/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilter.java b/src/main/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilter.java
new file mode 100644
index 000000000..39a6f3ffe
--- /dev/null
+++ b/src/main/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilter.java
@@ -0,0 +1,108 @@
+package com.hubspot.jinjava.lib.filter;
+
+import static com.hubspot.jinjava.lib.filter.ReplaceFilter.checkLength;
+
+import com.google.re2j.Matcher;
+import com.google.re2j.Pattern;
+import com.google.re2j.PatternSyntaxException;
+import com.hubspot.jinjava.doc.annotations.JinjavaDoc;
+import com.hubspot.jinjava.doc.annotations.JinjavaParam;
+import com.hubspot.jinjava.doc.annotations.JinjavaSnippet;
+import com.hubspot.jinjava.interpret.InvalidArgumentException;
+import com.hubspot.jinjava.interpret.InvalidInputException;
+import com.hubspot.jinjava.interpret.InvalidReason;
+import com.hubspot.jinjava.interpret.JinjavaInterpreter;
+import com.hubspot.jinjava.interpret.TemplateSyntaxException;
+import com.hubspot.jinjava.objects.SafeString;
+
+@JinjavaDoc(
+  value = "Returns true if the value matches the given regular expression (Java RE2 syntax), " +
+  "false otherwise. Uses partial matching (the pattern can match anywhere in the string). " +
+  "Anchor with ^...$ for full-string matching.",
+  input = @JinjavaParam(
+    value = "s",
+    desc = "Base string to test against",
+    required = true
+  ),
+  params = {
+    @JinjavaParam(
+      value = "regex",
+      desc = "The regular expression to match against the string",
+      required = true
+    ),
+  },
+  snippets = {
+    @JinjavaSnippet(
+      code = "{% if \"It costs $300\"|matches_regex(\"[0-9]+\") %}\n" +
+      "    Contains a number\n" +
+      "{% endif %}"
+    ),
+    @JinjavaSnippet(
+      desc = "Anchor the pattern to match the entire string",
+      code = "{% if \"hello\"|matches_regex(\"^[a-z]+$\") %}\n" +
+      "    All lowercase letters\n" +
+      "{% endif %}"
+    ),
+  }
+)
+public class MatchesRegexFilter implements Filter {
+
+  @Override
+  public String getName() {
+    return "matches_regex";
+  }
+
+  @Override
+  public Object filter(Object var, JinjavaInterpreter interpreter, String... args) {
+    if (args.length < 1) {
+      throw new TemplateSyntaxException(
+        interpreter,
+        getName(),
+        "requires 1 argument (regex string)"
+      );
+    }
+
+    if (args[0] == null) {
+      throw new TemplateSyntaxException(
+        interpreter,
+        getName(),
+        "requires a valid regex param (not null)"
+      );
+    }
+
+    if (var == null) {
+      return false;
+    }
+
+    String s;
+    if (var instanceof String) {
+      s = (String) var;
+    } else if (var instanceof SafeString) {
+      s = ((SafeString) var).getValue();
+    } else {
+      throw new InvalidInputException(interpreter, this, InvalidReason.STRING);
+    }
+
+    // Minor optimization, avoid checking short strings
+    if (s.length() > 100) {
+      checkLength(interpreter, s, this);
+    }
+
+    String regex = args[0];
+
+    try {
+      Pattern p = Pattern.compile(regex);
+      Matcher matcher = p.matcher(s);
+
+      return matcher.find();
+    } catch (PatternSyntaxException e) {
+      throw new InvalidArgumentException(
+        interpreter,
+        this,
+        InvalidReason.REGEX,
+        0,
+        regex
+      );
+    }
+  }
+}
diff --git a/src/test/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTestTest.java b/src/test/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTestTest.java
new file mode 100644
index 000000000..f39406c87
--- /dev/null
+++ b/src/test/java/com/hubspot/jinjava/lib/exptest/IsStringMatchingRegexExpTestTest.java
@@ -0,0 +1,74 @@
+package com.hubspot.jinjava.lib.exptest;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import com.google.common.collect.ImmutableMap;
+import com.hubspot.jinjava.BaseJinjavaTest;
+import com.hubspot.jinjava.objects.SafeString;
+import java.util.Arrays;
+import org.junit.Test;
+
+public class IsStringMatchingRegexExpTestTest extends BaseJinjavaTest {
+
+  private static final String MATCHING_TEMPLATE =
+    "{{ var is string_matching_regex arg }}";
+
+  @Test
+  public void itReturnsTrueForMatchingRegex() {
+    assertThat(
+      jinjava.render(
+        MATCHING_TEMPLATE,
+        ImmutableMap.of("var", "It costs $300", "arg", "[0-9]+")
+      )
+    )
+      .isEqualTo("true");
+  }
+
+  @Test
+  public void itReturnsFalseForNonMatchingRegex() {
+    assertThat(
+      jinjava.render(
+        MATCHING_TEMPLATE,
+        ImmutableMap.of("var", "hello world", "arg", "[0-9]+")
+      )
+    )
+      .isEqualTo("false");
+  }
+
+  @Test
+  public void itReturnsFalseForNull() {
+    assertThat(jinjava.render(MATCHING_TEMPLATE, ImmutableMap.of("var", "testing")))
+      .isEqualTo("false");
+  }
+
+  @Test
+  public void itWorksForSafeString() {
+    assertThat(
+      jinjava.render(
+        MATCHING_TEMPLATE,
+        ImmutableMap.of("var", "testing", "arg", new SafeString("^test"))
+      )
+    )
+      .isEqualTo("true");
+  }
+
+  @Test
+  public void itWorksWithSelectattr() {
+    String template =
+      "{% for item in items|selectattr('name', 'string_matching_regex', '^foo') %}{{ item.name }},{% endfor %}";
+    assertThat(
+      jinjava.render(
+        template,
+        ImmutableMap.of(
+          "items",
+          Arrays.asList(
+            ImmutableMap.of("name", "foobar"),
+            ImmutableMap.of("name", "baz"),
+            ImmutableMap.of("name", "foobaz")
+          )
+        )
+      )
+    )
+      .isEqualTo("foobar,foobaz,");
+  }
+}
diff --git a/src/test/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilterTest.java b/src/test/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilterTest.java
new file mode 100644
index 000000000..cfee8cfc5
--- /dev/null
+++ b/src/test/java/com/hubspot/jinjava/lib/filter/MatchesRegexFilterTest.java
@@ -0,0 +1,87 @@
+package com.hubspot.jinjava.lib.filter;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.assertThatThrownBy;
+
+import com.hubspot.jinjava.BaseInterpretingTest;
+import com.hubspot.jinjava.Jinjava;
+import com.hubspot.jinjava.JinjavaConfig;
+import com.hubspot.jinjava.interpret.InvalidArgumentException;
+import com.hubspot.jinjava.interpret.InvalidInputException;
+import com.hubspot.jinjava.objects.SafeString;
+import org.junit.Before;
+import org.junit.Test;
+
+public class MatchesRegexFilterTest extends BaseInterpretingTest {
+
+  MatchesRegexFilter filter;
+
+  @Before
+  public void setup() {
+    filter = new MatchesRegexFilter();
+  }
+
+  @Test
+  public void expects1Arg() {
+    assertThatThrownBy(() -> filter.filter("foo", interpreter))
+      .hasMessageContaining("requires 1 argument");
+  }
+
+  @Test
+  public void expectsNotNullArg() {
+    assertThatThrownBy(() -> filter.filter("foo", interpreter, new String[] { null }))
+      .hasMessageContaining("a valid regex");
+  }
+
+  @Test
+  public void itReturnsFalseOnNullInput() {
+    assertThat(filter.filter(null, interpreter, "foo")).isEqualTo(false);
+  }
+
+  @Test
+  public void itMatchesRegex() {
+    assertThat(filter.filter("It costs $300", interpreter, "[0-9]+")).isEqualTo(true);
+  }
+
+  @Test
+  public void itDoesNotMatchRegex() {
+    assertThat(filter.filter("hello world", interpreter, "[0-9]+")).isEqualTo(false);
+  }
+
+  @Test
+  public void itMatchesAnchoredRegex() {
+    assertThat(filter.filter("hello", interpreter, "^[a-z]+$")).isEqualTo(true);
+  }
+
+  @Test
+  public void itDoesNotMatchAnchoredRegex() {
+    assertThat(filter.filter("hello123", interpreter, "^[a-z]+$")).isEqualTo(false);
+  }
+
+  @Test(expected = InvalidArgumentException.class)
+  public void itThrowsExceptionOnInvalidRegex() {
+    filter.filter("It costs $300", interpreter, "[");
+  }
+
+  @Test
+  public void itMatchesRegexForSafeString() {
+    assertThat(filter.filter(new SafeString("It costs $300"), interpreter, "[0-9]+"))
+      .isEqualTo(true);
+  }
+
+  @Test
+  public void itLimitsLongInput() {
+    assertThatThrownBy(() ->
+        filter.filter(
+          "a".repeat(101),
+          new Jinjava(JinjavaConfig.newBuilder().withMaxStringLength(10).build())
+            .newInterpreter(),
+          "O"
+        )
+      )
+      .isInstanceOf(InvalidInputException.class)
+      .hasMessageContaining(
+        "Invalid input for 'matches_regex': input with length '101' exceeds maximum allowed length of '10'"
+      );
+  }
+}